Entire home
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
3 bedrooms2 bathroomsSleeps 10
Popular amenities
Explore the area

Chestertown, MD
- Place, Kings Town Park3 min drive
- Place, Roundtop Park3 min drive
- Place, Washington College4 min drive
- Airport, Baltimore, MD (MTN-Martin State)110 min drive
Rooms & beds
3 bedrooms (sleeps 10)
Bedroom 2
1 Queen Bed
Bedroom 3
1 Single Bunk Bed and 1 Queen Bed
Bedroom with river view
1 King Bed and 2 Single Beds
2 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Spaces
Porch or lanai
Kitchen
Outdoor play area
Garden
About this property
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end throughout the year. The home is also located just a short bike ride to Historic Chestertown, or you can even take one of our kayaks in while you enjoy the Chester River's rich wildlife.
Guests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings.
The three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun.
Minutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!
Chestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food.
About 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River.
With so many things to enjoy, book your experience today!
**Sheets are provided and beds made, but please bring towels**
Guests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings.
The three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun.
Minutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!
Chestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food.
About 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River.
With so many things to enjoy, book your experience today!
**Sheets are provided and beds made, but please bring towels**
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- Hot tub
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (107 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs (limit 2 total)
Please do not allow your pets on the furniture.
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
About the area
Chestertown
Located in Chestertown, this holiday home is in the city centre and on the beach. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Travelling with kids? Consider Crumpton Auction and The Mainstay. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Chestertown, MD
What's nearby
- Kings Town Park - 3 min drive - 1.8 km
- Roundtop Park - 3 min drive - 1.8 km
- Washington College - 4 min drive - 3.8 km
- Dover Downs Casino - 54 min drive - 63.8 km
- Dover International Speedway - 58 min drive - 64.2 km
Getting around
Restaurants
- Milano's Pizzeria - 6 min drive
- Royal Farms - 5 min drive
- Dunkin - 7 min drive
- McDonald's - 7 min drive
- Royal Farms - 5 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
11 Dec, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Dec 2025
Verified
10/10 Excellent
Cory F.
11 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cory F.
Stayed 3 nights in Jan 2026
Verified
10/10 Excellent
Betsy W.
25 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Betsy W.
Stayed 2 nights in Sep 2025
Verified
10/10 Excellent
Michael F.
27 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Michael F.
Stayed 3 nights in Oct 2025
Verified
10/10 Excellent
Michael F.
2 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy



Michael F.
Stayed 4 nights in Dec 2025
Verified
10/10 Excellent
victoria g.
10 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend getaway
victoria g.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Shaun S.
26 Oct, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was perfect
Shaun S.
Stayed 3 nights in Oct 2021
Verified
10/10 Excellent
Andrew M.
25 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Location
Andrew M.
Stayed 2 nights in May 2025
Verified
10/10 Excellent
Suzan B.
30 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Suzan B.
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
Hardeep S.
30 Jan, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and hours
Hardeep S.
Stayed 2 nights in Jan 2022
Verified
10/10 Excellent
David D.
3 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great family spot
David D.
Stayed 2 nights in Mar 2023
Verified
10/10 Excellent
Carter F.
12 Jan, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend with friends
Carter F.
Stayed 2 nights in Jan 2025
Verified
10/10 Excellent
Jason S.
30 Sept, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
Jason S.
Stayed 2 nights in Sep 2024
Verified
10/10 Excellent
Sean & Jasmine R.
17 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent peaceful scenic stay
Sean & Jasmine R.
Stayed 3 nights in Aug 2021
Verified
10/10 Excellent
Doug B.
5 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great to work with owners
Doug B.
Stayed 2 nights in Jul 2021
Verified
10/10 Excellent
Andrew E.
31 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and nice house
Andrew E.
Stayed 4 nights in Jan 2023
Verified
10/10 Excellent
Bryn M.
22 Apr, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend getaway
Bryn M.
Stayed 2 nights in Apr 2024
Verified
10/10 Excellent
Michael F.
27 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Idyllic River Getaway
Michael F.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
Emily L.
19 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
Emily L.
Stayed 2 nights in Apr 2023
Verified
10/10 Excellent
Debbie R.
10 Nov, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property on the water . House was well equipped -welcoming to guests , great place !!
Debbie R.
Stayed 2 nights in Oct 2022
Verified
10/10 Excellent
Amy K.
9 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amy K.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Michael F.
22 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another relaxing stay at this bucolic riverfront getaway
Michael F.
Stayed 3 nights in Apr 2023
Verified
10/10 Excellent
Kathryn W.
30 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great weekend!
Kathryn W.
Stayed 3 nights in May 2023
Verified
10/10 Excellent
Patricia D.
23 Jul, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown rental
Patricia D.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
Cindy D.
3 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Place on the River in Chestertown
Cindy D.
Stayed 2 nights in May 2024
About the host
Hosted by Ina Herrera
Being able to provide our renters with a place to relax and rejuvenate is our goal, the way it does for us when we visit with our own family.
Languages:
English, Spanish, Norwegian
Premier Host
They consistently provide great experiences for their guests
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